Reaction #90512

Reaction equation

5-bromo-6-methoxy-2,3-dihydro-1H-inden-1-one

morpholine

cesium carbonate

BINAP

→

crude compound 13

6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Solvents

toluene

Conditions

Workup

1. 1
   OtherThe reaction was degassed
2. 2
   Otherpurged with nitrogen for 10 min
3. 3
   Otherdegassed
4. 4
   Otherpurged and with nitrogen for another 10 min
5. 5
   Otherunder sealed microwave vial
6. 6
   workup.ADDITIONAfter completion of the starting material, the reaction was diluted with chloroform
7. 7
   Filtrationfiltered through celite bed
8. 8
   ConcentrationThe organic layer was concentrated

Procedure

A solution of 5-bromo-6-methoxy-2,3-dihydro-1H-inden-1-one (11) (1 g, 4.149 mmol) and morpholine (0.36 g, 4.149 mmol) in toluene 15 mL was added cesium carbonate (2.69 g, 8.298 mmol). The reaction was degassed and purged with nitrogen for 10 min. Pd2(dba)3 (189.3 mg, 0.207 mmol) and BINAP (64.5 mg, 0.103 mmol) was added, degassed and purged and with nitrogen for another 10 min. The reaction was heated to 110° C. overnight under sealed microwave vial. After completion of the starting material, the reaction was diluted with chloroform and filtered through celite bed. The organic layer was concentrated to get the crude compound 13 and the resulting crude was purified through flash chromatography by using 100-200 mesh silica gel eluting the compound at 25% ethyl acetate in hexane as pale yellow coloured solid 6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 13. 1HNMR (400 MHz, CDCl3) δ ppm 7.70 (s, 1H), 7.20 (s, 1H), 3.93 (s, 3H), 3.06 (m, 2H), 2.72 (m, 2H); MS (ESI) m/z 247.9 (M+H).

Source